Synthesis of Phosphoryl and Thiophosphoryl Compounds from Sulfur Dioxide and Phosphorus Compounds with a Coordination Number of Three

✍ Scribed by Doz. Dr. E. Fluck; H. Binder

• Publisher: John Wiley and Sons
• Year: 1965
• Tongue: English
• Weight: 121 KB
• Volume: 4
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196503591

✦ Synopsis

a-Formylc~clo/iexurtrune: A solution of 73 g of dimethylforniamide in 300 g of dichloromethane is stirred with exclusion of moisture at 5-10°C, and a solution of 100 g of phosgene in 300 g of dichloromethane is added dropwise. The mixture is left standing for 3 h, and then 167 g of I-morpholinocyclohexene are added gradually with stirring at room temperature. The solution is heated for 30 min at about 40 OC under reflux; 400 g of ice water are then added, and the whole is left standing overnight. The products are extracted with ether, the ether extract is washed several times with water, dried with sodium sulfate, and concentrated in VOCIIO. The residue is vacuum distilled over a Vigreux column 30 cm long, yielding 65 g of a-formylcyclohexanone as an oil (n?; = 1.5128) which rapidly turns brown. It reacts exothermally with aniline in dimethylformamide to yield the anil, m.p. 151 "C from dimethylformamide.